3,4-dihydro-2H-pyran → 1-Bromo-2-(tetrahydropyran-2-yl)oxypropane

HRID 246047Notes

Reaction equation

HRID 246047 reaction equation
[Br:1][CH2:2][CH:3]([OH:5])[CH3:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.CCOC(C)=O>[Br:1][CH2:2][CH:3]([CH3:4])[O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 297401-Bromo-2-propanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 156249911-Bromo-2-(tetrahydropyran-2-yl)oxypropane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-bromopropan-2-ol (1.25 g, 9.0 mmol) and 3,4-dihydro-2H-pyran (2.04 ml, 22.5 mmol) in dichloromethane (50 ml) at 0° C. was added p-toluenesulfonic acid monohydrate (85 mg, 0.45 mmol). The reaction mixture was stirred at 0° C. for 15 min then warmed to room temperature and stirred for 2 h. The reaction was diluted with EtOAc and washed with water, sat NaHCO3, and brine then dried over MgSO4 and concentrated to afford 2-(2-bromo-1-methyl-ethoxy)-tetrahydro-2H-pyran as a light brown oil which was used without further purification.

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred for 2 h
  3. washwashed with water
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb1f2cb6c8564b27ae97aa80722f7066
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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